US3784601A - Process for the production of molded articles or coatings from polyadducts by reaction of polyethers with polyisocyanates - Google Patents

Process for the production of molded articles or coatings from polyadducts by reaction of polyethers with polyisocyanates Download PDF

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Publication number
US3784601A
US3784601A US00227256A US3784601DA US3784601A US 3784601 A US3784601 A US 3784601A US 00227256 A US00227256 A US 00227256A US 3784601D A US3784601D A US 3784601DA US 3784601 A US3784601 A US 3784601A
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US
United States
Prior art keywords
production
polyethers
coatings
polyether
molded articles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00227256A
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English (en)
Inventor
K Jellinek
R Oellig
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rain Carbon Germany GmbH
Original Assignee
Ruetgerswerke AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ruetgerswerke AG filed Critical Ruetgerswerke AG
Application granted granted Critical
Publication of US3784601A publication Critical patent/US3784601A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4887—Polyethers containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4875—Polyethers containing cyclic groups containing cycloaliphatic groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31605—Next to free metal

Definitions

  • This invention relates to the use of polyethers, which carry hydroxyl groups and have a cycloaliphatic base structure, for the production of molded articles or coatings.
  • Aromatic polyethers containing hydroxyl groups are known in the art. They can be produced, for example, by condensation of bivalent phenols with diepoxy compounds in a molar ratio of about 1:1 with the aid of a catalyst. Solid products with variable molecular weights are obtained.
  • the polyethers have a linear structure, and carry hydroxyl groups in the chain and at the ends of the chain.
  • the diglycidylether of bisphenol A and 4,4- dihydroxydiphenyl methane have been found to be particularly suitable as the phenolic component of the condensation reaction.
  • the resulting high molecular weight polyethers are particularly suitable as binders in varnishes and adhesive compositions
  • the polyethers are surprisingly resistant to chemical attack by acids, caustics, and organic solvents. Also, they exhibit a high degree of adhesion to almost all metallic, inorganic and organic substances.
  • these aromatic polyethers have been found to be important components in the production of protective coatings for surfaces where corrosion resistance is important.
  • Aromatic polyethers are generally dissolved in suitable solvents. By cross-linking the polyethers with polyisocyanates, varm'shes are obtained which can be used under hot or cold conditions.
  • Component A G. (1) Polyether described under (a) dissolved in cyclohexanone to obtain a solution having a 40% solids content 52.9 (2) Titanium white RN 57 14.2 (3) Blanc fixe N 7.1 (4) Microtalc AT extra 7.1
  • Components (1) through (4) are dispersed in a ball mill to obtain a particle size below 10p.
  • This varnish when applied to a metal substrate with a brush or spray gun, will result in a film having the following characteristics.
  • the resin prepared in this manner has the following characteristics Softening range C-.. 80-85 Content of hydroxyl groups percent 6 (b) Production and characteristics of the varnish:
  • the polyether is melted on a heated two-roll mill at a roll temperature of -110 C., and is mixed with the filler. After the filler has been Well wetted and distributed homogeneously, the agent for the formation of the adduct is added, and this is mixed at the same temperature for 1-2 minutes. Subsequently the mixture is immediately cooled, and the mixture at first is preground in a disk attrition mill, it being further comminuted afterwards in an impeller breaker. A screened grain fraction of 30-80 is suitable for use as a coating powder and can be applied with the customary application device. The material is suitable both for operating with an electrostatic spray gun and in fluidized beds, as customary in whirl sintering.
  • composition of matter comprising the reaction product of a polyether and a polyisocyanate, the improvement wherein the polyether has the formula:
  • R" unsubstituted, halogen-substituted or alkyl substituted cyclohexylene ring
  • R" cyclohexylene, tricyclodecane-dimethylene or cyclohexanedimethylene
  • n an integer from about 10 to about 40.
  • composition of claim 1 in which the polyether is the reaction product of an unsubstituted, halogen-substituted or alkyl substituted hexahydrophthalic acid diglycidyl ester with a cycloaliphatic diol in a molar ratio of 1:0.8 to 0.821, the value of n of the polyether being determined by the reaction of said ester with said diol.
  • composition of claim 3 in which the diol is selected from the group consisting of 4,4'-dihydroxydicyclohexylpropane and tricyclodecanedimethylol.
  • composition of claim 1 in which the polyisocyanate is tris-(isocyanatohexamethylene)-biuret.
  • a coating composition comprising as essential filmforming component the composition of claim 1.
  • a molded article comprised of the composition of claim 1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
US00227256A 1971-02-17 1972-02-17 Process for the production of molded articles or coatings from polyadducts by reaction of polyethers with polyisocyanates Expired - Lifetime US3784601A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2107441A DE2107441C3 (de) 1971-02-17 1971-02-17 Verfahren zum Herstellen von Formteilen oder Überzügen aus Polyaddukten durch Umsetzen von Polyäthern mit Estergruppierungen mit Polyisocyanaten

Publications (1)

Publication Number Publication Date
US3784601A true US3784601A (en) 1974-01-08

Family

ID=5798957

Family Applications (1)

Application Number Title Priority Date Filing Date
US00227256A Expired - Lifetime US3784601A (en) 1971-02-17 1972-02-17 Process for the production of molded articles or coatings from polyadducts by reaction of polyethers with polyisocyanates

Country Status (10)

Country Link
US (1) US3784601A (enrdf_load_stackoverflow)
AT (1) AT323424B (enrdf_load_stackoverflow)
BE (1) BE779507A (enrdf_load_stackoverflow)
CH (1) CH561752A5 (enrdf_load_stackoverflow)
DE (1) DE2107441C3 (enrdf_load_stackoverflow)
DK (1) DK143762C (enrdf_load_stackoverflow)
FR (1) FR2125574B1 (enrdf_load_stackoverflow)
IT (1) IT948371B (enrdf_load_stackoverflow)
NL (1) NL7201669A (enrdf_load_stackoverflow)
SE (1) SE382993B (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4163087A (en) * 1974-09-12 1979-07-31 Politechnika Warszawska Method for production of new thermal and chemical resistant polyurethane plastics
US4273913A (en) * 1979-03-26 1981-06-16 W. R. Grace & Co. Isocyanate capped urethane-containing prepolymer prepared from polyols obtained from epihalohydrin
US4297482A (en) * 1979-12-13 1981-10-27 W. R. Grace & Co. Chain-extended polyol compositions and method
CN111675803A (zh) * 2020-07-28 2020-09-18 清远高新华园科技协同创新研究院有限公司 一种含有刚性环状结构的无溶剂羟基树脂及其制备方法

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4163087A (en) * 1974-09-12 1979-07-31 Politechnika Warszawska Method for production of new thermal and chemical resistant polyurethane plastics
US4273913A (en) * 1979-03-26 1981-06-16 W. R. Grace & Co. Isocyanate capped urethane-containing prepolymer prepared from polyols obtained from epihalohydrin
US4297482A (en) * 1979-12-13 1981-10-27 W. R. Grace & Co. Chain-extended polyol compositions and method
CN111675803A (zh) * 2020-07-28 2020-09-18 清远高新华园科技协同创新研究院有限公司 一种含有刚性环状结构的无溶剂羟基树脂及其制备方法
CN111675803B (zh) * 2020-07-28 2023-01-17 清远高新华园科技协同创新研究院有限公司 一种含有刚性环状结构的无溶剂羟基树脂及其制备方法

Also Published As

Publication number Publication date
DK143762B (da) 1981-10-05
CH561752A5 (enrdf_load_stackoverflow) 1975-05-15
NL7201669A (enrdf_load_stackoverflow) 1972-08-21
FR2125574B1 (enrdf_load_stackoverflow) 1975-10-24
AT323424B (de) 1975-07-10
DE2107441A1 (de) 1972-08-31
DK143762C (da) 1982-03-15
SE382993B (sv) 1976-02-23
DE2107441B2 (de) 1973-10-18
IT948371B (it) 1973-05-30
DE2107441C3 (de) 1974-05-16
FR2125574A1 (enrdf_load_stackoverflow) 1972-09-29
BE779507A (fr) 1972-06-16

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